Retro‐Friedel‐Crafts‐Type Acidic Ring‐Opening of Triptycenes: A New Synthetic Approach to Acenes

The triptycene scaffold has been ring‐opened by using a retro‐Friedel‐Crafts‐type reaction under acidic conditions to give its corresponding anthrone product. 9‐Hydroxytriptycenes and unsubstituted triptycene undergo ring‐opening reaction under strongly acidic conditions, such as with TfOH. An inves...

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Bibliographic Details
Published in:Chemistry : a European journal 2022-02, Vol.28 (12), p.e202104160-n/a
Main Authors: Iwata, Takayuki, Kawano, Ryusei, Fukami, Takuto, Shindo, Mitsuru
Format: Article
Language:English
Subjects:
acenes
anthrones
Chemistry
Friedel-Crafts reaction
retro-Friedel-Crafts reaction
ring-opening reaction
Substitution reactions
triptycenes
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Summary:The triptycene scaffold has been ring‐opened by using a retro‐Friedel‐Crafts‐type reaction under acidic conditions to give its corresponding anthrone product. 9‐Hydroxytriptycenes and unsubstituted triptycene undergo ring‐opening reaction under strongly acidic conditions, such as with TfOH. An investigation of the substitution effect has revealed that the electron‐donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA. In addition, the reaction has been successfully applied toward the synthesis of tetracene. The triptycene scaffold has been ring‐opened in a retro‐Friedel‐Crafts‐type reaction under acidic conditions to give its corresponding anthrone product. 9‐Hydroxytriptycenes and unsubstituted triptycene undergo ring‐opening reaction under strongly acidic conditions, such as with TfOH. An investigation of the substitution effect has revealed that the electron‐donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA. In addition, the reaction has been successfully applied toward the synthesis of tetracene.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202104160